Maryland taxes are a bit of a weird beast. Most states just have a flat or progressive state tax and call it a day. In Maryland, we have the "piggyback" system. Basically, you’re paying the state, and then you’re paying your specific county (or Baltimore City) on top of that. If you’re self-employed, a freelancer, or just someone with a lot of investment income, you’ve probably realized by now that nobody is taking those taxes out for you.
You have to pay Maryland estimated taxes yourself.
Honestly, it’s easy to mess up. If you wait until April to settle the bill, the Comptroller of Maryland will likely hit you with interest and penalties. It’s not just about the money you owe; it’s about when you give it to them.
Who actually needs to pay?
The rule is pretty straightforward but easy to ignore. If you expect your Maryland tax liability to be more than $500 after you subtract your withholdings and credits, you’re on the hook for estimated payments.
This happens a lot with:
- Gig workers (Uber, DoorDash, freelance designers).
- People with significant rental income.
- Investors who sold stocks for a big gain.
- Business owners (LLCs, S-Corps, Sole Proprietorships).
If you’re a W-2 employee and you have a side hustle, you might be able to avoid this by just asking your boss to withhold more from your "day job" paycheck. But for most of us, quarterly vouchers are the reality.
The 2026 Deadlines: Don't miss these
The state doesn't care if you're "busy." They want their cut four times a year. For the 2026 tax year, the dates are standard, but if the 15th falls on a weekend, it pushes to the next business day.
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- April 15, 2026 (1st Quarter)
- June 15, 2026 (2nd Quarter)
- September 15, 2026 (3rd Quarter)
- January 15, 2027 (4th Quarter)
Fun fact: If you file your full Maryland return by January 31, 2027, and pay the whole balance, you can actually skip that final January 15th estimated payment. It’s a nice way to save a step if you’re an early bird.
How to pay Maryland estimated taxes without losing your mind
You’ve got options. Some are digital and fast; others involve stamps and envelopes.
The iFile and Maryland Tax Connect Portals
Maryland has been moving everything toward their new system called Maryland Tax Connect. By 2026, this is the primary hub. It's actually pretty decent once you get past the registration. You can set up a direct debit from your bank account (E-check), which is free.
Credit Cards
You can use a credit card, but why would you? The state uses third-party processors like Official Payments or NICUSA, and they charge a service fee—usually around 2.45%. Unless you’re trying to hit a massive sign-on bonus for a new card, that fee usually eats up any rewards you'd earn.
The Paper Route (Form 502D)
If you’re old school, you’ll need Form 502D, the Declaration of Estimated Tax Vouchers. You print them out, fill in your info, and mail them to the Comptroller in Annapolis.
Important Note: Make your check payable to "Comptroller of Maryland." Always write your Social Security Number and "2026 Form 502D" in the memo line. If that check gets separated from your voucher, you’ll want the state to know whose account to credit.
New rules you should know about
Governor Moore signed some changes recently that affect higher earners. If you’re making over $500,000 (or $600,000 for joint filers), your state tax rate has bumped up. We’re looking at 6.25% for that bracket, and it hits 6.5% if you’re over a million.
There's also a new 2% surtax on capital gains if your federal adjusted gross income (AGI) is over $350,000. These aren't just "rich people problems"—they affect how much you need to send in every quarter to avoid an underpayment penalty.
Avoiding the "Underpayment Interest" trap
The Comptroller is actually kinda strict. To stay safe, you generally need to pay at least 90% of your current year’s tax or 110% of what you paid last year (the "Safe Harbor" rule).
If you paid $5,000 in Maryland taxes last year, and you pay $5,500 in equal installments this year, you’re usually safe from penalties, even if you actually ended up owing $10,000 because your business blew up. It’s a lifesaver for people with fluctuating income.
Actionable Next Steps
Don't wait until the deadline to figure this out.
- Check your 2025 return. Look at your total Maryland tax (usually line 28 or 29 on Form 502). Divide that by four. That’s a solid starting point for your 2026 payments.
- Set up a Maryland Tax Connect account. It’s much easier than mailing paper vouchers every three months.
- Set calendar reminders. Put them in your phone for the 10th of April, June, September, and January so you have a five-day lead time.
- Account for county rates. Remember that places like Montgomery County or Howard County have higher local rates (up to 3.2% or 3.3%) than more rural areas. Your estimated payment must cover both state and local portions.
If you get stuck, the Comptroller’s office actually answers the phone. You can call 1-800-MD-TAXES. Just don't call them on April 14th; the hold times are legendary.